Guanidinium 8-hydroxy-7-iodo­quinoline-5-sulfonate monohydrate

The crystal structure of guanidinium 8-hydroxy-7-iodo­quino­line-5-sulfonate monohydrate, [(CH₆N₃⁺)₂(C₉H₄INO₄S^2-)·H₂O], shows a three-dimensional hydrogen-bonded polymer structure, in which the two guanidinium cations and the water mol­ecule are involved in extensive hydrogen bonding, linking together rows of the dianions. The dianions result from deprotonation of both the sulfonic acid and the phenolic hydroxy groups of the substituted quinoline mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.095
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C2       =      13.71 su
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1B    ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N11    -   H11A     =       0.74 Ang.
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N12    -   H12A     =       0.72 Ang.
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N13    -   H13B     =       0.71 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

(I)

Crystal data

2CH6N3^+·C9H4INO4S^−·H2O	F(000) = 968
Mr = 487.28	Dx = 1.829 Mg m^−3
Monoclinic, P21/a	Melting point = 441–445 K
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.7107 Å
a = 22.329 (2) Å	Cell parameters from 25 reflections
b = 6.9918 (19) Å	θ = 12.5–16.1°
c = 11.3456 (8) Å	µ = 1.97 mm^−1
β = 92.646 (7)°	T = 295 K
V = 1769.4 (5) Å^3	Plate, pale brown
Z = 4	0.50 × 0.50 × 0.20 mm

Data collection

Rigaku AFC7R diffractometer	3559 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.022
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
ω–2θ scans	h = −10→28
Absorption correction: ψ scan TeXsan for Windows (Molecular Structure Corporation, 1999)'	k = 0→9
Tmin = 0.398, Tmax = 0.674	l = −14→14
4344 measured reflections	3 standard reflections every 150 reflections
4057 independent reflections	intensity decay: 18.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 2.4019P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.018
4057 reflections	Δρmax = 1.32 e Å^−3
275 parameters	Δρmin = −1.19 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I7	0.234933 (10)	−0.20393 (3)	0.419865 (19)	0.0396 (1)
S5	0.41595 (3)	0.24664 (12)	0.21790 (7)	0.0286 (2)
O8	0.15677 (10)	0.1141 (4)	0.2775 (2)	0.0375 (7)
O51	0.42226 (11)	0.2538 (4)	0.0902 (2)	0.0371 (7)
O52	0.43580 (11)	0.4257 (4)	0.2724 (2)	0.0403 (7)
O53	0.44545 (10)	0.0795 (4)	0.2715 (2)	0.0391 (7)
N1	0.19050 (12)	0.4417 (4)	0.1663 (2)	0.0351 (8)
C2	0.20755 (16)	0.6037 (6)	0.1100 (3)	0.0438 (10)
C3	0.26662 (16)	0.6509 (6)	0.0988 (3)	0.0403 (10)
C4	0.31098 (15)	0.5298 (5)	0.1417 (3)	0.0357 (9)
C5	0.33875 (13)	0.2197 (4)	0.2409 (3)	0.0284 (8)
C6	0.31982 (13)	0.0601 (5)	0.2996 (3)	0.0293 (8)
C7	0.25883 (13)	0.0276 (4)	0.3150 (2)	0.0280 (8)
C8	0.21333 (13)	0.1474 (5)	0.2685 (2)	0.0275 (8)
C9	0.29593 (13)	0.3570 (5)	0.1969 (2)	0.0279 (8)
C10	0.23374 (14)	0.3180 (4)	0.2092 (2)	0.0275 (8)
N11	0.07177 (14)	0.4162 (5)	0.0563 (3)	0.0401 (9)
N12	0.03364 (16)	0.2393 (6)	−0.1001 (3)	0.0418 (10)
N13	0.07837 (16)	0.0913 (5)	0.0622 (3)	0.0425 (10)
C11	0.06209 (14)	0.2483 (5)	0.0046 (3)	0.0311 (8)
N21	0.06664 (16)	0.3266 (5)	0.3711 (3)	0.0440 (10)
N22	0.09874 (18)	0.1422 (6)	0.5282 (4)	0.0551 (11)
N23	0.00221 (18)	0.2601 (7)	0.5170 (4)	0.0533 (11)
C21	0.05587 (16)	0.2394 (5)	0.4719 (3)	0.0365 (9)
O1W	0.07994 (15)	0.7867 (5)	0.2855 (3)	0.0653 (11)
H2	0.177400	0.686500	0.077200	0.0520*
H3	0.277000	0.767400	0.061700	0.0480*
H4	0.351800	0.562600	0.133800	0.0430*
H6	0.348600	−0.0294	0.330100	0.0350*
H11A	0.093 (2)	0.421 (7)	0.108 (4)	0.044 (12)*
H11B	0.0686 (18)	0.513 (6)	0.012 (3)	0.035 (10)*
H12A	0.0259 (19)	0.327 (6)	−0.131 (4)	0.031 (11)*
H12B	0.026 (2)	0.140 (8)	−0.128 (4)	0.053 (14)*
H13A	0.0973 (19)	0.095 (7)	0.130 (4)	0.046 (11)*
H13B	0.0788 (19)	0.003 (7)	0.031 (4)	0.036 (11)*
H21A	0.093 (3)	0.281 (8)	0.335 (5)	0.061 (16)*
H21B	0.038 (3)	0.370 (8)	0.327 (5)	0.066 (15)*
H22A	0.091 (2)	0.076 (7)	0.579 (4)	0.050 (13)*
H22B	0.128 (3)	0.133 (8)	0.491 (5)	0.060 (15)*
H23A	−0.005 (2)	0.207 (7)	0.587 (5)	0.058 (14)*
H23B	−0.025 (3)	0.321 (9)	0.474 (6)	0.08 (2)*
H1A	0.107 (3)	0.891 (9)	0.285 (6)	0.066 (15)*
H1B	0.105 (4)	0.681 (9)	0.293 (7)	0.076 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I7	0.0391 (2)	0.0376 (2)	0.0421 (2)	−0.0032 (1)	0.0016 (1)	0.0130 (1)
S5	0.0225 (3)	0.0317 (4)	0.0314 (4)	−0.0011 (3)	0.0003 (3)	−0.0016 (3)
O8	0.0233 (10)	0.0446 (13)	0.0445 (12)	−0.0013 (10)	0.0021 (9)	0.0071 (11)
O51	0.0362 (12)	0.0427 (12)	0.0330 (11)	0.0010 (10)	0.0082 (9)	−0.0011 (10)
O52	0.0353 (12)	0.0396 (13)	0.0457 (13)	−0.0076 (10)	−0.0028 (10)	−0.0075 (11)
O53	0.0258 (11)	0.0402 (13)	0.0509 (13)	0.0014 (10)	−0.0036 (9)	0.0063 (11)
N1	0.0291 (13)	0.0392 (15)	0.0365 (13)	0.0049 (11)	−0.0030 (10)	0.0074 (12)
C2	0.0320 (16)	0.053 (2)	0.0450 (18)	0.0159 (16)	−0.0121 (14)	−0.0071 (16)
C3	0.0432 (19)	0.0364 (17)	0.0417 (17)	0.0015 (14)	0.0057 (14)	0.0125 (15)
C4	0.0320 (15)	0.0393 (17)	0.0363 (15)	0.0011 (13)	0.0061 (12)	0.0066 (13)
C5	0.0247 (13)	0.0335 (15)	0.0271 (13)	0.0004 (11)	0.0009 (11)	−0.0006 (11)
C6	0.0282 (14)	0.0319 (15)	0.0276 (13)	0.0023 (12)	−0.0013 (11)	0.0023 (12)
C7	0.0303 (14)	0.0298 (14)	0.0238 (12)	−0.0011 (12)	0.0003 (10)	0.0024 (11)
C8	0.0260 (14)	0.0343 (15)	0.0222 (12)	−0.0016 (12)	0.0017 (10)	−0.0026 (11)
C9	0.0281 (14)	0.0315 (15)	0.0240 (12)	0.0032 (12)	0.0004 (10)	0.0003 (11)
C10	0.0281 (14)	0.0306 (15)	0.0234 (12)	0.0031 (11)	−0.0017 (10)	0.0002 (11)
N11	0.0391 (16)	0.0363 (16)	0.0440 (16)	−0.0010 (13)	−0.0082 (13)	0.0017 (14)
N12	0.0471 (18)	0.0424 (18)	0.0349 (15)	0.0042 (15)	−0.0077 (13)	−0.0007 (15)
N13	0.0548 (19)	0.0331 (16)	0.0392 (16)	0.0045 (14)	−0.0024 (14)	0.0025 (14)
C11	0.0240 (14)	0.0369 (16)	0.0323 (14)	0.0007 (12)	0.0018 (11)	0.0004 (13)
N21	0.0361 (16)	0.0521 (19)	0.0438 (16)	0.0065 (14)	0.0026 (14)	0.0074 (15)
N22	0.0442 (19)	0.067 (2)	0.054 (2)	−0.0010 (18)	0.0011 (16)	0.0229 (19)
N23	0.0421 (19)	0.068 (2)	0.051 (2)	−0.0082 (18)	0.0144 (16)	−0.0114 (19)
C21	0.0312 (16)	0.0401 (17)	0.0381 (16)	−0.0070 (13)	−0.0004 (13)	−0.0050 (14)
O1W	0.0522 (18)	0.073 (2)	0.070 (2)	−0.0202 (16)	−0.0062 (15)	0.0143 (17)

Geometric parameters (Å, º)

I7—C7	2.093 (3)	N23—C21	1.332 (5)
S5—O51	1.463 (2)	N21—H21B	0.85 (6)
S5—O52	1.456 (3)	N21—H21A	0.80 (6)
S5—O53	1.460 (3)	N22—H22A	0.77 (5)
S5—C5	1.765 (3)	N22—H22B	0.80 (6)
O8—C8	1.293 (4)	N23—H23B	0.87 (7)
O1W—H1B	0.93 (7)	N23—H23A	0.90 (6)
O1W—H1A	0.94 (5)	C2—C3	1.371 (5)
N1—C10	1.369 (4)	C3—C4	1.375 (5)
N1—C2	1.363 (5)	C4—C9	1.409 (5)
N11—C11	1.326 (5)	C5—C9	1.429 (4)
N12—C11	1.322 (5)	C5—C6	1.376 (5)
N13—C11	1.320 (5)	C6—C7	1.400 (4)
N11—H11B	0.84 (4)	C7—C8	1.401 (4)
N11—H11A	0.74 (5)	C8—C10	1.453 (4)
N12—H12B	0.78 (5)	C9—C10	1.428 (4)
N12—H12A	0.72 (4)	C2—H2	0.9506
N13—H13A	0.86 (4)	C3—H3	0.9505
N13—H13B	0.71 (5)	C4—H4	0.9481
N21—C21	1.328 (5)	C6—H6	0.9507
N22—C21	1.315 (5)
O51—S5—O52	110.47 (15)	S5—C5—C6	118.8 (2)
O51—S5—O53	112.18 (15)	S5—C5—C9	121.3 (2)
O51—S5—C5	106.82 (15)	C5—C6—C7	121.0 (3)
O52—S5—O53	112.86 (15)	C6—C7—C8	123.3 (3)
O52—S5—C5	108.00 (14)	I7—C7—C6	118.1 (2)
O53—S5—C5	106.13 (14)	I7—C7—C8	118.5 (2)
H1A—O1W—H1B	103 (6)	C7—C8—C10	115.3 (3)
C2—N1—C10	118.9 (3)	O8—C8—C7	123.8 (3)
C11—N11—H11B	116 (3)	O8—C8—C10	120.8 (3)
H11A—N11—H11B	118 (5)	C4—C9—C5	124.2 (3)
C11—N11—H11A	119 (4)	C4—C9—C10	117.4 (3)
C11—N12—H12B	120 (4)	C5—C9—C10	118.4 (3)
H12A—N12—H12B	121 (5)	N1—C10—C8	116.9 (3)
C11—N12—H12A	119 (4)	C8—C10—C9	121.9 (3)
C11—N13—H13B	119 (4)	N1—C10—C9	121.2 (3)
H13A—N13—H13B	117 (5)	N1—C2—H2	118.77
C11—N13—H13A	122 (3)	C3—C2—H2	118.95
C21—N21—H21B	121 (4)	C4—C3—H3	119.87
C21—N21—H21A	115 (4)	C2—C3—H3	120.17
H21A—N21—H21B	113 (6)	C3—C4—H4	119.84
H22A—N22—H22B	125 (5)	C9—C4—H4	119.97
C21—N22—H22B	112 (4)	C7—C6—H6	119.54
C21—N22—H22A	120 (3)	C5—C6—H6	119.50
C21—N23—H23B	117 (4)	N11—C11—N12	120.1 (3)
C21—N23—H23A	120 (3)	N11—C11—N13	118.8 (3)
H23A—N23—H23B	123 (5)	N12—C11—N13	121.0 (4)
N1—C2—C3	122.3 (3)	N21—C21—N22	119.9 (4)
C2—C3—C4	120.0 (4)	N21—C21—N23	118.9 (4)
C3—C4—C9	120.2 (3)	N22—C21—N23	121.1 (4)
C6—C5—C9	119.9 (3)
O51—S5—C5—C6	119.5 (3)	S5—C5—C6—C7	−176.9 (2)
O51—S5—C5—C9	−58.6 (3)	C6—C5—C9—C10	−3.7 (4)
O52—S5—C5—C6	−121.6 (3)	C5—C6—C7—C8	2.9 (5)
O52—S5—C5—C9	60.2 (3)	C5—C6—C7—I7	−173.9 (2)
O53—S5—C5—C6	−0.3 (3)	I7—C7—C8—O8	−6.5 (4)
O53—S5—C5—C9	−178.5 (2)	C6—C7—C8—O8	176.7 (3)
C10—N1—C2—C3	−2.6 (5)	C6—C7—C8—C10	−4.2 (4)
C2—N1—C10—C8	180.00 (1)	I7—C7—C8—C10	172.62 (17)
C2—N1—C10—C9	0.6 (4)	O8—C8—C10—N1	1.4 (4)
N1—C2—C3—C4	2.2 (5)	O8—C8—C10—C9	−179.3 (2)
C2—C3—C4—C9	0.2 (5)	C7—C8—C10—C9	1.6 (4)
C3—C4—C9—C5	178.0 (3)	C7—C8—C10—N1	−177.8 (2)
C3—C4—C9—C10	−2.0 (4)	C4—C9—C10—N1	1.6 (4)
C9—C5—C6—C7	1.3 (5)	C5—C9—C10—N1	−178.4 (3)
S5—C5—C9—C4	−5.6 (4)	C5—C9—C10—C8	2.3 (4)
S5—C5—C9—C10	174.4 (2)	C4—C9—C10—C8	−177.7 (3)
C6—C5—C9—C4	176.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O8^i	0.95 (6)	1.92 (6)	2.865 (4)	175 (6)
N11—H11A···N1	0.74 (5)	2.25 (4)	2.883 (4)	144 (4)
N11—H11B···O51^ii	0.84 (4)	2.06 (4)	2.894 (4)	169 (4)
N12—H12A···O53^ii	0.72 (4)	2.48 (4)	3.121 (5)	148 (4)
N12—H12B···O52^iii	0.78 (5)	2.41 (5)	3.036 (5)	139 (4)
N13—H13A···O8	0.86 (4)	2.09 (4)	2.943 (4)	170 (4)
N13—H13B···O51^iii	0.71 (5)	2.22 (5)	2.925 (4)	171 (5)
N21—H21A···O8	0.80 (6)	1.98 (6)	2.754 (4)	165 (6)
N21—H21B···O53^iv	0.85 (6)	2.16 (7)	2.958 (4)	156 (6)
N22—H22A···O52^v	0.77 (5)	2.10 (5)	2.858 (5)	172 (5)
N22—H22B···O8	0.80 (6)	2.54 (6)	3.186 (5)	139 (6)
N23—H23A···O1W^vi	0.90 (6)	2.26 (5)	2.979 (6)	137 (4)
N23—H23B···O53^iv	0.87 (7)	2.46 (7)	3.209 (5)	144 (6)
C4—H4···O52	0.9481	2.5758	3.180 (4)	121.91
C6—H6···O53	0.9507	2.4148	2.841 (4)	106.93

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z; (iii) −x+1/2, y−1/2, −z; (iv) x−1/2, −y+1/2, z; (v) −x+1/2, y−1/2, −z+1; (vi) −x, −y+1, −z+1.